If every rep had a digital coworker to prep calls, update CRM, and draft perfect follow-ups—what would your team do with the time back? Robert Henderson (Head of Revenue, AskElephant) breaks down AI orchestration for sales & CS, why “proactive AI” beats prompt-and-pray, and how leaders can coach in near-real-time.

What you’ll learn:

• What an AI orchestration platform actually does for sellers, CS, and leaders
• How custom agents (“digital workers”) automate prep, notes, CRM hygiene, and follow-ups
• Building a deal-intervention agent that alerts managers when a call goes sideways
• The future: proactive AI that acts before you ask
• The leadership system Robert uses: a Personal Priority Roadmap aligned to company goals
• Big mistakes teams make rolling out AI—and how to avoid siloed chaos

Key takeaways:

• AI should make humans more human: deepen connection & decision-making.
• Treat agents as digital workers you hire/train to your playbook.
• Move from reactive “prompting” to proactive AI aligned to your customer journey.
• Align leadership with a public personal roadmap to enforce focus.

Resources mentioned:

Multipliers by Liz Wiseman

Designing Your Life by Bill Burnett & Dave Evans

Connect with Robert Henderson https://www.linkedin.com/in/robert-henderson/
Connect with AskElephant: https://www.askelephant.ai/

Connect with Rick Smith https://www.linkedin.com/in/rick-smith-094b29b
Connect with Conquer https://conquer.io/

#Sales #CustomerSuccess #AIinSales #RevenueOperations #SalesLeadership #SalesAI #ProactiveAI #DigitalWorkers #AIAgents #CRMAutomation #RevOps #AskElephant

In this episode of The Future of Selling, host Rick Smith is joined by Michael Gallagher, founder of the Stevie Awards and co-founder of two AI-driven companies: Reqsy and ImageShield.

Michael shares why recognition matters more than ever in an AI-powered world, how storytelling is the key to standing out, and why building your personal brand is crucial—especially for early-career sales professionals facing automation threats.

🔥 Key Topics:

Why Michael launched the "Oscars for Business" in the shadow of Enron

How AI is changing sales recognition—and how to use it wisely

How to tell a story that gets noticed (and wins awards)

Advice for sales reps who want to future-proof their careers

💡 Whether you’re a seller, a team leader, or just curious about the future of recognition and AI, this conversation will leave you with clear, practical takeaways.

Connect with Michael Gallagher https://www.linkedin.com/in/michael-gallagher-a8b785/
Nominate a Sales Pro for a Stevie Award: https://stevieawards.com//sales

Connect with Rick Smith https://www.linkedin.com/in/rick-smith-094b29b
Connect with Conquer https://conquer.io/

Cold outreach is broken—and this founder has a plan to fix it.
In this episode of The Future of Selling, we explore what happens when you stop spamming inboxes and start respecting your prospects.

Our guest is Ryan O'Hara, founder of Pitchfire, a paid-prospecting platform that flips traditional sales outreach on its head. Instead of begging for time, reps pay for responses—and it’s working. With reply rates up to 60% and meetings booked in just 3 pitches, this is not your average cold outreach conversation.

🎯 We cover:
– Why reply rates have plummeted and how to turn the tide
– The difference between buying a meeting vs. buying a response
– How creativity (like sending piano songs!) builds trust
– What “zero-click marketing” and personal branding mean for sellers
– Why paid prospecting could actually be more ethical
– The future of B2B sales, AI, and buyer-led deal rooms
– A real story about how a cold call led to a life-changing conversation

Whether you lead a sales team or carry a quota, this conversation will challenge the way you think about outreach.

Connect with Ryan O'Hara https://www.linkedin.com/in/ryanmohara/
Connect with Pitchfire https://www.pitchfire.com/

Connect with Rick Smith https://www.linkedin.com/in/rick-smith-094b29b
Connect with Conquer https://conquer.io/

In this episode of The Future of Selling Podcast, host Rick Smith sits down with Shannon Schaul, founder and principal of SKS Advisory, to explore how sales has fundamentally changed since the pandemic, and what leaders must do to adapt.

Shannon brings a unique perspective from years of building go-to-market strategies for growth-stage, mission-driven companies. From empathy-driven selling to the rise of hybrid sales skills, this conversation covers it all.

• What’s different about selling in 2025
• Why empathy and small talk are essential, not optional
• The outdated sales mindsets that no longer work
• Why your team must use their voice
• The problem with most sales training, and how to fix it
• How to invest in people the right way
• And why "hitting pause" might be the most powerful leadership move you can make

Whether you're a CRO, sales leader, or individual contributor, this episode is packed with practical insights to help you lead with purpose and perform at a higher level.

Connect with Shannon Schaul: https://www.linkedin.com/in/shannonschaul/

Connect with Rick Smith: https://www.linkedin.com/in/rick-smith-094b29b/
Check out Conquer: https://conquer.io/

When a deal closes, the real work begins—but only if sales and client success are aligned. In this episode of The Future of Selling, host Rick Smith sits down with award-winning client success leader Erica Newell to explore the underestimated power of a well-executed sales handoff.

Erica brings wisdom from years of customer success leadership, sharing why bad handoffs lead to churn, how “turf anxiety” kills collaboration, and what great teams do to build trust across the client lifecycle. You'll learn:

• The top 3 pitfalls of poor sales-CS transitions
• How to create a frictionless baton pass
• Why early involvement of CS (especially in enterprise deals) is essential
• Which metrics matter—and which don’t
• How to build client relationships that endure beyond contracts

Whether you're a CRO, CSM, or sales leader, this episode is packed with practical strategies to create smoother handoffs, happier clients, and healthier revenue.

Connect with Erica Newell: https://www.linkedin.com/in/ericajnewell/

Connect with Rick Smith: https://www.linkedin.com/in/rick-smith-094b29b/

Check out Conquer: https://conquer.io/

What if the key to scaling your company wasn’t a new strategy, but a new way of being?

In this provocative and insightful episode, executive coach and sales transformation architect Townsend Wardlaw joins us to unpack why consciousness, not just systems or hustle, is the most powerful growth lever a founder can use. From his bold take on integrity and mindset to the hidden meaning behind "yes" and "no" in sales conversations, Townsend offers a radical reframe for how leaders can drive revenue, align teams, and ultimately create companies built for a high-value exit.

🔥 What You’ll Learn:

• Why consciousness is more than mindset and how it drives tangible business outcomes
• How founders unintentionally become bottlenecks, and what to do about it
• The game-changing difference between playing to win vs. not to lose
• What it really means to lead with integrity, and how it accelerates revenue
• Why checking for understanding is a secret superpower in leadership
• A simple, powerful step to shift your company’s trajectory—starting today

About Townsend Wardlaw:

Townsend is a coach, consultant, and advisor to founders, helping companies between $1M and $10M scale revenue and create meaningful exits. He’s known for challenging leaders to elevate their consciousness and shift their results by changing how they see and show up in the world.

Connect with Townsend Wardlaw: https://www.linkedin.com/in/townsendwardlaw/

Connect with Rick Smith: https://www.linkedin.com/in/rick-smith-094b29b/
Check out Conquer: https://conquer.io/

In this episode, Rick talks discusses the evolving landscape of sales enablement with Brian Trautschold, co-founder of Ambition, a leading sales performance management platform.

Brian shares his entrepreneurial journey—from coffee runs and copy machines at UBS to co-founding multiple startups and building Ambition into a company that transforms sales teams through coaching, gamification, and trust.

If you're a sales leader navigating the complexities of scaling your team or thinking about how AI and manager enablement will shape the next decade of performance, this is a must-listen conversation.

Connect with Brian Trautschold: https://www.linkedin.com/in/brian-trautschold-97518219/
Check out Ambition: https://ambition.com/

Connect with Rick Smith: https://www.linkedin.com/in/rick-smith-094b29b/
Check out Conquer: https://conquer.io/

In this high-energy and deeply insightful episode, Rick sits down with Amanda Rubin, Chief Revenue Officer at Wildfire and former EVP of Growth at Enthusiast Gaming. Together, they explore how authenticity is reshaping modern marketing, particularly through Amanda’s groundbreaking work connecting brands with communities on Discord.

Amanda explains how Wildfire is helping brands authentically integrate into Gen Z-focused communities—not through ads, but through meaningful dialogue, partnerships, and experiences. She also unpacks the difference between marketing vs. branding, why trust is the ultimate competitive advantage, and how startups should think about go-to-market strategy from day one.

In the second half of the episode, Amanda opens up about building her career as a woman in a male-dominated industry, overcoming imposter syndrome, and how she’s found purpose by blending strategic leadership with human connection. Her story is as real as her leadership style—and one that will resonate with professionals at every level.

🎧 Tune in for a masterclass in modern brand building—and how character and competence create career momentum.

Connect with Amanda Rubin: https://www.linkedin.com/in/amanda-j-rubin/
Check out Wildfire: https://www.getwildfire.gg/

Connect with Rick Smith: https://www.linkedin.com/in/rick-smith-094b29b/
Check out Conquer: https://conquer.io/